Vat dyestuffs



Patented May 12, 1931 outrun-Tres- PAT WALTER MIEG, or VOHW'INKEL, NEAR ELBERFELD', ennmAivg ssrelvon TO GENERAL ANILINE woaxs, me, or NEW YORK, 1v. Y., A CORPORATION or DELAWARE o VAT DYESTUFFS No Drawing. Ap lication filed October 27, 1927,.Seria1 No. 229,274, and in Germany November 4, 1926.

The present invention concerns new vat dyestufis of the anthraquinone series of the probable formula 1 O H C acylamino group and a process for their production. They are obtained by causing sulfuric acid to act at a lowtemperature on di- ,7

anthraquinonylamines, containing at least one acridone ring and in addition at least one acylamino group or on the derivatives and substitution products of such bodies and oxidizing the resulting condensation products, whenever necessary, I

In accordance with the invention dianthraquinonylamines of the kind indicated, as for example containing at least one acridone ring in the 3 t-position are converted into differently colored compounds possessing valuable dyeing properties by prolonged heating of the respective solutions in sulfuric acid to about 80 to 40 C. The action is similar to that described in U. S. Patent 996,109. It is possible to proceed also by subjecting the substances in question to short treatment with sulfuric acid at a still lower temperature followed by oxidation of the intermediate product thus obtained. Compare U. S. patent application Ser. No. 119,197. Without A zene or aniline with an olive to blue coloration. They are valuable vat dyestuffs possessing very good fastness, properties.

The following example will illustrate my EwampZe: 10 parts weight of the di anthraquinonylamine derivative, i obtained by the condensation of one molecule of 4-an1- ino-l:2-anthraquinone acridone with one molecule of l-benzoylamino-5 chloro-anthraquinone are dissolved in 100 parts by weight of concentrated sulfuric acid at about 15 to 20 C. Thesolution which is orange colored at first very quicklybecomes an olive tinged rown. On stirring the solution into water, a grass-green precipitate is obtained, which ecomes olive brown on the-addition of about o parts by Weight of sodium nitrite. By heatng to about 60 C. a dyestuif is obtained, havmg most probably the formula:

OFFICE 1 brown vat, dissolving in sulfuric acid with a deep blue coloration and dyeing fast olive tinged brown shades on cotton, while the starting material vatted in the form of a f powder dyes cotton a greenish-grey color.

By replacing in the above example l-benzoyl amino 5 chloro-anthraquinone by 1- benzol amino 4 chloro anthraquinone, a reddish-grey vat dyestuff which forms a yellow-brown vat is obtained in a similar manner from the starting material which. dyes greyish green shades.

I claim: V 1 Asa new product a vat dyestufi having most probably theformulaz p 7 NH o Of -00 C n 5, 0 NH'J o t" I I oancoNH i 7 being a dark powder soluble in concentrated B5 sulfuric-acid'with a deep blue coloration sololi'veti'nged brown shades. I p

'2, The process which comprises causing 40 of the probable general formula} zoylamino group, but at least one X being a benzoylamino group at a temperature between about 15 to about40 C. and oxidizing the condensation product thus obtained.

ubl'e in boiling nitrobenzene with an olivecoloration; dyeing cotton from the vat fast strong sulfuric acid to .act, upon a compound 3.. 'I he process which comprises. causing strong sulfuric acid to act upon a compound of the probable formula:

at a temperature between about 15 to about 20 C. and oxidizing the condensation product; thus obtained.

4. As new products-vat dyestuffs of the probable general formula:

uo x, V

wherein X stands for hydrogen. or the benzoyl-amino group, at. least one X being a benzoyl-amino group, said products forming dark powders, difficulty soluble in the usualv organic solvents, dyeing cotton from a yellow-brown vat olive-brown to reddish-grey shades of good fastness-properties.

Intestimony whereof I have hereunto set my hand.

WALTER MIEG.

l IQ. 

